Are The Astros Missing The Window For Extensions?

One of the more interesting developments this offseason, even if it didn’t capture too much fanfare then, was Hunter Brown’s hiring of Scott Boras as his new agent. Chandler Rome of The Athletic reported earlier this year that the Astros and Brown had “mutual interest” around this time a year ago before the latter’s successful 2024 season, a poor April notwithstanding. With Boras now in charge of securing Brown’s large payday after 2028, it stands to wonder if Houston missed their best chance to sign their second-best starter to an extension. If so, it is another miss by the club’s front office in recent years on the extension front.

Extensions have long been a curious topic surrounding the Astros. Dana Brown was bold in interviews when first hired in February 2023, creating anticipation that multiple extensions were possibly incoming. I mean, it doesn’t take much to connect the dots when coming from the Braves, known for their ability to sign their young stars before entering free agency.

The obvious candidates at the time of his hiring — Alex Bregman, Kyle Tucker, and Framber Valdez — were perhaps all unrealistic in hindsight. Bregman, for example, already signed one below-market extension in March 2019. The odds of him signing a second one with a new general manager were always a pipe dream. Tucker and Valdez, both scheduled to enter free agency upon the conclusion of the 2025 season, could’ve been more plausible, but that ship likely sailed pretty early on in Brown’s tenure in 2023. Tucker’s impending free agency in light of Juan Soto’s record-breaking contract eventually forced the Astros’ hand for the first time in this era of contention, trading him away for something other than allowing him to walk away for a comp pick next offseason. The front office also explored trading Valdez before Tucker was dealt to the Cubs.

(As a side note, Tucker isn’t matching Soto’s contract. But it isn’t unrealistic to expect an offer approaching at least $400 million for the star outfielder).

Thus far in Dana Brown’s tenure, the organization has only signed extensions with two players: Cristian Javier and Jose Altuve. But considering Brown’s frankness regarding extensions throughout his first season on the job, the organization’s lack of movement on non-Altuve extensions has become noticeable. To be fair to Brown, though, Crane’s seeming reluctance to offer contracts more than half a decade in length has thwarted those extension efforts more than his general manager regarding the trio of Bregman, Tucker, and Valdez. This ownership group has generally avoided long-term contracts beyond five years. Perhaps six years, but the AAV has to work for them. With that said, it doesn’t help the perception of extension assurances when the general manager makes comments like this one, and then you trade that same player a little over a year later.

The Astros, however, have other players that are likely worth extending. For an organization that is light on top prospects, it would be prudent to lock up some of these younger players while the farm system is being rebuilt. You can’t keep letting go of existing talent when the pipeline isn’t producing at the same rate as before.

• Hunter Brown (free agent after 2028)
• Bryan Abreu (free agent after 2026)
• Jeremy Peña (free agent after 2027)
• Yainer Díaz (free agent after 2028)
• Spencer Arrighetti (free agent after 2029)

Of the five players I listed above, an extension to Díaz and Arrighetti is possibly the most realistic, considering the time between now and the end of their arbitration-eligible seasons. Probably more so the latter than the former, considering Arrighetti’s Houston ties, but I guess one can hope for both. In the case of Abreu, he is scheduled to enter free agency in less than two years. Josh Hader has four more years left on his contract, so I don’t think the Astros will be anxious to spend heavily to keep him. Of course, I didn’t expect them to spend big on Hader, so never say never. Peña is an interesting case, as I think his performance this upcoming season will hold quite a bit of sway over his future earnings. Brice Matthews’ development will also remain a factor.

Hunter Brown is far less certain. He’s also arguably the most important. Again, Boras is his agent, and his clients are extensively not known for signing team-friendly extensions. However, this isn’t a universal truth with Boras clients (see the original extensions for Altuve and Bregman). Like Díaz, Brown isn’t scheduled to enter free agency until the conclusion of the 2028 World Series. There’s still ample time to get an extension done. But, again, the Astros likely missed their best chance last year, at least on more favorable terms for the club. Suppose Brown’s success carries over into 2025, and he sets himself up as the ace of the staff in 2026. In that case, those odds will likely drop even lower, and it’ll be a poor look on the front office for missing another opportunity to keep homegrown talent.

Here’s the thing, though: The Astros don’t have to exceed five to six years in extensions, much less ten, to extend most of these players. They already have the template with Altuve’s and Bregman’s original extensions of five to six years, buying out a couple of free agent years. James Click did that same very thing with Yordan Alvarez’s extension. Yes, it takes two to tango in negotiations. However, there are ways of accomplishing extensions without breaking this franchise’s cardinal rule regarding the terms of an offer.

There is still time for Brown to fulfill some of his extension promises. Valdez is still with the club to start the 2025 season, so there’s always hope, no matter how faint, that an agreement can be reached. Personally, I doubt it, but I’d gladly be wrong. I’d also imagine quite a few younger players are interested in staying long-term if the offer is fair. However, the lack of movement on this front since Altuve’s extension over a year ago has become increasingly noticeable. It’s not dire in any sense, but it’s worth monitoring in the near future as Brown enters his third season as general manager.